Syntheses of IAA- and IPA-amino acid conjugates.
Amino acid derivatives of IAA and IPA are prepared conveniently and efficiently by coupling of readily available 2a-b with diverse free amino acids 3a-g and (3c+3c') to give compounds 4a-j, (4c+4c') and (4h+4h') in 38-70% yields. Similarly, 2a-b afforded IAA and IPA peptide conjugates 6a-b in 32-40% yields. Complete retention of chirality was supported by NMR and HPLC analysis.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Khelashvili
Levan
L
Munawar
Munawar Ali
MA
D000596:Amino Acids / Q000737:chemistry*; D007210:Indoleacetic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry
D000596:Amino Acids; D007210:Indoleacetic Acids; D007211:Indoles; D011422:Propionates; D014230:Triazoles; C030737:indoleacetic acid; C012771:benzotriazole; C095446:3-(indol-3-yl)propionic acid